How the wealthy save billions in taxes by skirting a century-old law

By Paul Kiel and Jeff Ernsthausen and ProPublica

Series: The Secret IRS Files Inside the Tax Records of the .001%

At first glance, July 24, 2015, seems to have been a brutal trading day for Steve Ballmer, the former Microsoft CEO. He dumped hundreds of stocks, losing at least $28 million.

But this was no panicked sell-off. Among the stocks Ballmer sold were those of the Australian mining company BHP and the global oil giant Shell. Had Ballmer lost confidence in BHP’s management? Was he betting that the price of oil would not soon recover? Not at all. That very day, Ballmer also bought thousands of shares in BHP and Shell.

Why would he sell and buy shares in the same companies on the same day? The answer is counterintuitive to the average person but obvious to a sophisticated investor: A loss, for tax purposes, is valuable; a big one can wipe out millions in potential taxes. Ballmer’s two-step process allowed him to use the loss to lower his taxes, while the near-simultaneous purchase meant he effectively hadn’t changed his investment.

Since 1921, claiming tax losses from so-called wash sales — selling shares of a company then buying them again within a short period — has been forbidden. But Ballmer collected his losses anyway because, technically, the types of shares he bought and sold weren’t the same.

Both Shell and BHP offered two different versions of their common stock. For each company, the two stocks were legally distinct, but they performed very similarly because, after all, they were shares in the same company.

Ballmer’s not-so-bad day, in fact, was carefully planned, part of a strategy by Goldman Sachs, which conducted the trades on Ballmer’s behalf, to wield the stock market’s natural volatility to the billionaire’s advantage. At Goldman, the hundreds of stocks in Ballmer’s “Tax Advantaged Loss Harvesting” accounts were selected to follow the movement of the broader markets. Over time, the markets, as they had historically, would buoy Ballmer’s investments upward. When, inevitably, some of the stocks underperformed or the whole market dipped, Goldman was ready to pounce, selling off the losers and replacing them with equivalents.

Sometimes, the replacements were nearly identical securities, as with Shell and BHP. More often, they were not. But well-tuned software could easily find the right stocks to keep the accounts tracking the market. His losses secured, Ballmer was ready to catch the bounce back.

Over and over, Ballmer sold and bought stocks in roughly equivalent amounts, as on that July day, when he swapped around $200 million worth. A month later, he did it again, landing at least $23 million in tax-reducing losses. Similar efforts that December brought $26 million more.

ProPublica estimates that from 2014 through 2018, Ballmer was able to generate tax losses totaling $579 million without changing his investment portfolio in a meaningful way. The tax savings from these losses amount to at least $138 million.

The scale of Goldman’s feat was remarkable, but Ballmer was just one client pursuing such a strategy. And Goldman was just part of an industry that helps the ultrawealthy report billions in losses — and save billions in potential taxes — even as their fortunes rise.

ProPublica was able to reconstruct the tax-loss strategies of scores of the nation’s wealthiest people, including Ballmer and Facebook co-founders Mark Zuckerberg and Dustin Moskovitz, using a trove of IRS data that has been the basis for “The Secret IRS Files” series. This trove includes not only some two decades of tax returns for thousands of the nation’s wealthiest citizens but also voluminous records of their trading.

After inquiries by ProPublica, Goldman said it would halt transactions like Ballmer’s Shell and BHP trades. Goldman conducted a review, according to a statement by the bank, and found that a “very small percentage” of its “tax investment solutions” trades were “inadvertently made in a manner inconsistent with our strategy.” The bank said it strives “to provide bestin-class investment advice